[Cl-].[Al+3].[Cl-].[Cl-].C(NB)(C)(C)C.[CH2:11]([O:13][C:14]([N:16]1[CH2:23][CH:22]2[CH:18]([CH2:19][C:20]3[C:26]([CH2:27]O)=[C:25]([Cl:29])[S:24][C:21]=32)[CH2:17]1)=[O:15])[CH3:12].[OH-].[Na+]>C(Cl)Cl>[CH2:11]([O:13][C:14]([N:16]1[CH2:23][CH:22]2[CH:18]([CH2:19][C:20]3[C:26]([CH3:27])=[C:25]([Cl:29])[S:24][C:21]=32)[CH2:17]1)=[O:15])[CH3:12]Aluminum chloride (131.7 mg, 0.990 mmol) was added to a round bottom flask, cooled to 0° C. and diluted with anhydrous CH2Cl2 (3.3 ml). Next, tert-butylaminoborane (172 mg, 1.98 mmol) was added and the contents were stirred for 30 minutes. A solution of 5-Chloro-6-hydroxymethyl-3,3a,7,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[α]pentalene-2-carboxylic acid ethyl ester (99.7 mg, 0.33 mmol) in CH2Cl2 (330 μl) was added to the AlC13/t-butylaminoborane complex. The reaction mixture slowly warmed to room temperature and stirred for 16 hours. Next, the contents were carefully poured into 15% NaOH and extracted with CH2Cl2 (2×50 ml). The organic layer was dried (MgSO4), solvent evaporated in vacuo, and the residue purified by preparative TLC (hexanes:EtOAc-7:3) to give the subtitle compound. MS calculated for C13H16ClNO2S+H 286, observed 286.
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